Front of Home
Front door to unit
Entrance Stairs
Kitchen
Closet in Kitchen area

The Blue House in Clearwater

2 bedrooms·1 bath
Clearwater • Florida

$3,559.50 USD total for 30 nights

Nov 7 – Dec 7, 2026

Gulf Breeze Getaway - Sand Key image 1
Gulf Breeze Getaway - Sand Key image 2
Gulf Breeze Getaway - Sand Key image 3
Gulf Breeze Getaway - Sand Key image 4
Gulf Breeze Getaway - Sand Key image 5

Gulf Breeze Getaway - Sand Key

2 bedrooms·2 baths
Clearwater • Florida

$5,650.00 USD total for 30 nights

Nov 7 – Dec 7, 2026

"If your in Clearwater don't think twice this place it is great!! Jack and Shelly really out did them self. My new home every time we come. Don't miss out!" - Cortney
Waterfront Condo | Steps to Clearwater Beach 2King
" My favorite place to be was the large patio, soaking in the sights and sounds of the bay. I definitely would love to go back!" - Kristine
"The place was gorgeous and well worth the price." - Rob
"My family very much enjoyed our stay in Clearwater beach and waking up to the gorgeous views of Clearwater Bay. The unit was large and very clean with a lot of helpful items (many kitchen utensils and products, beach towels and chairs, games, etc). We were sad to leave!" - Sierra

Waterfront Condo | Steps to Clearwater Beach 2King

3 bedrooms·2 baths
Clearwater • Florida

$1,354.00 USD total for 3 nights

Nov 7 – 10, 2026

Harborview Grande #405
Harborview Grande #405
Harborview Grande #405
Harborview Grande #405
Harborview Grande #405

Harborview Grande #405

3 bedrooms·2 baths
Clearwater • Florida
5(71 reviews)

$2,145.95 USD total for 4 nights

Nov 7 – 11, 2026

Start your morning with coffee on your private balcony overlooking the peaceful harbor.
Bright, comfortable living room with beautiful harbor views and plenty of space to relax.
KING + TWIN bedroom with a dedicated workspace—flexible sleeping for families plus room to work.
Private KING bedroom with TV, ceiling fan, charging stations and plenty of storage.
Heated waterfront pool and sundeck overlooking the harbor—perfect after a day at the beach.

Dock of the Bay, #204 Walk Everywhere • Harbor Views • 2 King Suites

2 bedrooms·2 baths
Clearwater • Florida
5(210 reviews)

$1,023.42 USD total for 3 nights

Nov 9 – 12, 2026

Welcome to Dock Holiday! Bright waterfront living with beautiful harbor views and Clearwater Beach just a 5-minute walk away.
Relax on your private balcony overlooking the harbor—perfect for morning coffee or an evening glass of wine.
Private KING bedroom with TV, ceiling fan, charging stations and plenty of storage.
Two QUEEN beds make this spacious second suite ideal for families, friends, or groups who want comfortable sleeping arrangements and plenty of room.
Enjoy the heated bayfront swimming pool and sundeck—perfect for swimming, lounging, and relaxing with beautiful harbor views.

Dock Holiday, #205 Walk to Beach! Pool + Free Parking + Beach Gear

2 bedrooms·2 baths
Clearwater • Florida
5(198 reviews)

$1,125.62 USD total for 3 nights

Nov 29 – Dec 2, 2026

Dockside Duo = TWO complete side-by-side waterfront condos—perfect for families and friends traveling together.
Beautiful harbor views from your private balconies—start the morning with coffee by the water.
Condo #1 – Dock of the Bay: Spacious waterfront living room with sleeper sofa, Roku TV and Cable.
Condo #2 – Dock Holiday: Bright waterfront living room with sleeper sofa, Roku TV and Cable.
Condo #1 – Dock of the Bay: Comfortable KING bedroom with TV, ceiling fan, charging stations and ample storage.

Dockside Duo, #204 & #205 Side-by-Side Waterfront Condos | Walk to Beach

4 bedrooms·4 baths
Clearwater • Florida
5(7 reviews)

$2,812.07 USD total for 4 nights

Dec 7 – 11, 2026

Kitchen
A little piece of Beach House Heaven!
Waterfront Beach House Steps Away from #1 Beach!
Master Bedroom Balcony!
2nd floor (main living space) with gourmet kitchen and waterfront balcony attached!

Waterfront Beach House Steps Away from #1 Beach!

3 bedrooms·2 baths
Pinellas County • Florida
5(60 reviews)

$2,189.08 USD total for 3 nights

Nov 7 – 10, 2026

Sweet Craftsman home, free bikes, near beach & DT image 1
Sweet Craftsman home, free bikes, near beach & DT image 2
Sweet Craftsman home, free bikes, near beach & DT image 3
Sweet Craftsman home, free bikes, near beach & DT image 4
Sweet Craftsman home, free bikes, near beach & DT image 5

Adorable Private Craftsman

2 bedrooms·1 bath
Clearwater • Florida
4.86(267 reviews)

$562.00 USD $539.65 USD total for 3 nights

Nov 7 – 10, 2026

Bring your bike or enjoy the Complimentary bikes available. Actual model may varies. Pinellas trail is about 0.3 miles away, perfect for biking and walking.
Adorable Bungalow near beach, DT. Pet & Bike. image 2
Adorable Bungalow near beach, DT. Pet & Bike. image 3
Fully equipped kitchen.
Adorable Bungalow near beach, DT. Pet & Bike. image 5

Adorable Private Bungalow

2 bedrooms·1 bath
Clearwater • Florida
4.81(264 reviews)
$109 – $179/ night(excl. fees & taxes)
Sun Harbor Bay Haven-4 min walk to the beach, dog friendly
Sun Harbor Bay Haven-4 min walk to the beach, dog friendly
Sun Harbor Bay Haven-4 min walk to the beach, dog friendly
Sun Harbor Bay Haven-4 min walk to the beach, dog friendly
Sun Harbor Bay Haven-4 min walk to the beach, dog friendly

Sun Harbor Bay Haven-4 min walk to the beach, dog friendly

3 bedrooms·2½ baths
Clearwater • Florida
5(22 reviews)

$1,219.27 USD total for 3 nights

Nov 9 – 12, 2026

Water views,4m beach walk, boat dock, free parking
Water views,4m beach walk, boat dock, free parking
Water views,4m beach walk, boat dock, free parking
Water views,4m beach walk, boat dock, free parking
Water views,4m beach walk, boat dock, free parking

Water views,4m beach walk, boat dock, free parking

3 bedrooms·2½ baths
Clearwater • Florida
4.87(55 reviews)

$1,219.27 USD total for 3 nights

Nov 8 – 11, 2026

The Oaks at Keene Estate
The Oaks at Keene Estate
The Oaks at Keene Estate
The Oaks at Keene Estate
The Oaks at Keene Estate

The Oaks at Keene Estate

6 bedrooms·4 baths
Clearwater • Florida

$3,855.00 USD total for 4 nights

Mar 17 – 21, 2027

Oasis Paradise unit
Oasis Paradise unit
Oasis Paradise unit
Oasis Paradise unit
Oasis Paradise unit

Oasis Paradise unit

1 bedroom·1 bath
Clearwater • Florida

$447.00 USD total for 3 nights

Nov 7 – 10, 2026

BlueJay's Nest: Game Room, King Bed, Walk to Water image 2
BlueJay's Nest: Game Room, King Bed, Walk to Water image 1
BlueJay's Nest: Game Room, King Bed, Walk to Water image 3
BlueJay's Nest: Game Room, King Bed, Walk to Water image 4
BlueJay's Nest: Game Room, King Bed, Walk to Water image 5

BlueJay's Nest: Game Room, King Bed, Walk to Water

2 bedrooms·1 bath
Clearwater • Florida
5(30 reviews)

$8,079.50 USD $7,446.70 USD total for 28 nights

Nov 7 – Dec 5, 2026

BlueJay's Nest: private retreat w/ yard and patio image 1
BlueJay's Nest: private retreat w/ yard and patio image 2
Queen bed
BlueJay's Nest: private retreat w/ yard and patio image 4
Full bath with light-up mirror and extra supplies.

BlueJay's Nest: private retreat w/ yard and patio

2 bedrooms·1 bath
Clearwater • Florida
5(67 reviews)

$6,437.61 USD $5,933.90 USD total for 28 nights

Nov 7 – Dec 5, 2026

Where the view becomes your backdrop
Your waterfront pool retreat awaits
Welcome to The Lookout
Your beach escape begins inside

The Lookout

3 bedrooms·2 baths
Anna Maria • Florida
5(2 reviews)

$5,237.89 USD total for 7 nights

Nov 30 – Dec 7, 2026

Blissful pool and spa
Huge backyard paradise
Welcome to adorable Anna Margaritas
Come on in!
Welcoming open floor plan

Anna Margaritas

2 bedrooms·2 baths
Anna Maria • Florida

$3,087.60 USD total for 7 nights

Dec 8 – 15, 2026

Resort-style backyard retreat
Welcome to the Veranda on Jacaranda
Tropical vacation begins here

The Veranda on Jacaranda

4 bedrooms·3½ baths
Anna Maria • Florida

$4,301.22 USD total for 7 nights

Dec 4 – 11, 2026

Welcome to Luxe Island Escape
Multi-level decks overlooking the pool
Main foyer
Amazing views from every room

Luxe Island Escape

4 bedrooms·4½ baths
Anna Maria • Florida
5(1 review)

$6,334.58 USD total for 7 nights

Nov 10 – 17, 2026

Huge pool with attached spa
Welcome to Paradise Blu!
Huge tropical yard and pool
Grand living room with views

Paradise Blu

4 bedrooms·4½ baths
Anna Maria • Florida
5(2 reviews)

$5,842.24 USD total for 7 nights

Nov 15 – 22, 2026

Poolside backyard retreat
Kick back and relax poolside
Welcome to Bay Bungalow
Step inside the open living space
Recently updated interior with new furniture

Bay Bungalow

3 bedrooms·2 baths
Anna Maria • Florida

$3,058.06 USD total for 7 nights

Nov 29 – Dec 6, 2026

A pool unlike any other
Fun beyond the beach awaits
Welcome to Beachfront Bliss
Welcome to unforgettable island living
Open living area made for gathering

Beachfront Bliss

5 bedrooms·5½ baths
Anna Maria • Florida

$11,473.38 USD total for 7 nights

Nov 13 – 20, 2026

Margaritaville Pool Home
LR with two queen sleeper sofas with memory foam mattresses
LR with two queen sleeper sofas
LR and Dining area
LR and Ding area

Margaritaville Pool Home

3 bedrooms·2 baths
Clearwater • Florida
4.85(65 reviews)

$1,497.20 USD total for 3 nights

Nov 15 – 18, 2026